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[ CAS No. 7442-52-6 ]

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2D
Chemical Structure| 7442-52-6
Chemical Structure| 7442-52-6
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Product Details of [ 7442-52-6 ]

CAS No. :7442-52-6MDL No. :MFCD00667560
Formula : C12H12O3 Boiling Point : 319.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :204.22Pubchem ID :344494
Synonyms :

Computed Properties of [ 7442-52-6 ]

TPSA : 43.4 H-Bond Acceptor Count : 3
XLogP3 : 2.1 H-Bond Donor Count : 0
SP3 : 0.33 Rotatable Bond Count : 2

Safety of [ 7442-52-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7442-52-6 ]

  • Upstream synthesis route of [ 7442-52-6 ]
  • Downstream synthetic route of [ 7442-52-6 ]

[ 7442-52-6 ] Synthesis Path-Upstream   1~18

  • 1
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Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 11, p. 6225 - 6234
  • 2
  • [ 64-17-5 ]
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  • [ 6742-26-3 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 8, p. 1775 - 1778
  • 3
  • [ 614-45-9 ]
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  • [ 54125-61-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 11285 - 11289
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Reference: [1] Synlett, 2009, # 16, p. 2659 - 2662
  • 5
  • [ 7442-52-6 ]
  • [ 74-88-4 ]
  • [ 54125-61-0 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 24, p. 2859 - 2868
[2] Chemistry - A European Journal, 2008, vol. 14, # 9, p. 2699 - 2708
  • 6
  • [ 529-34-0 ]
  • [ 616-38-6 ]
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YieldReaction ConditionsOperation in experiment
100% With sodium hydride In methanol; mineral oil at 80℃; for 3 h; Inert atmosphere Under nitrogen atmo-sphere, α-tetralone (25.0 mmol, 3.33 mL), dimethyl carbonate (300 mmol, 25.0 mL), sodium hydride (60percent in mineral oil, 50.0 mmol, 2.00 g) and dry methanol (0.1 mL) are heated to 80 °C and stirred for 3 hours. After cooling, hydrochloric acid (3 N, 30.0 mL) is added, the mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate. After removing the solvent, 4 (5.06 g, 100percent) is obtained as a red-brown liquid.
92% Inert atmosphere; Reflux General procedure: A solution of α-tetralone (10 mmol) in dimethyl carbonate(5 mL) was added to a stirred suspension of NaH (60percent dispersion,15 mmol) in dimethyl carbonate (10 mL) under argon atmosphere.The solution was refluxed and once the reaction was judged completeafter a TLC test the solvent was evaporated. The resultant solid was dissolved in hydrochloric acid (2 M) and the phases were separated. The aqueous phase was extracted with ethyl acetate(35 mL). The organic extracts were dried (MgSO4) and evaporated to dryness. Flash chromatography (EtOAc/hexane 10percent) afforded the pure products. 4.2.1. Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate(5a).33 Yield 92percent; brown solid; mp66e68 C; Rf 0.35 (hexane/EtOAc 10/1). IR (KBr) (cm1): 2946; 2897; 1728; 1677; 1598; 1451;1372; 1313; 1156; 949; 900; 732; 1H NMR (CDCl3, 400 MHz) dH:12.41 (s, 1H), 8.04 (d, J7.9 Hz, 1H), 7.78 (d, J7.6 Hz, 1H), 7.47e7.43(m, 1H), 7.30e7.23 (m, 3H), 7.21 (d, J7.6 Hz, 1H), 7.13 (d, J7.1 Hz),3.79 (s, 3H), 3.75 (s, 3H), 3.59 (dd, J10.5, 4.7 Hz, 1H), 3.04e2.92 (m,2H), 2.77 (dd, J10.8, 4.6 Hz, 2H), 2.57e2.51 (m, 2H), 2.49e2.42 (m,1H), 2.34e2.29 (m, 1H); 13C NMR (CDCl3, 100 MHz) dC: 193.3, 173.2,170.7, 165.2, 143.8, 139.5, 134.0, 131.8, 130.6, 130.0, 128.9, 127.8,127.5, 127.0, 126.7, 124.4, 96.9, 54.5, 52.5, 51.8, 27.8, 27.7, 26.5, 20.6;MS (EI) m/z (percent): 204 (M), 189, 172, 144, 127, 118, 115, 90, 77, 63, 51.
92% Inert atmosphere; Reflux General procedure: A solution of the α-tetralone (10 mmol) in dimethyl carbonate (5 mL) was added to a stirred suspension of NaH (60percent dispersion, 15 mmol) in dimethyl carbonate (10 mL) under an atmosphere of argon. The solution was refluxed; when the reaction was complete (TLC monitoring) the solvent was evaporated. The resultant solid was dissolved in 2 M HCl and the phases were separated. The aqueous phase was extracted with EtOAc (3 × 15 mL). The organic extracts were dried (MgSO4) and evaporated to dryness. Flash chromatography (10percent EtOAc/hexane) afforded the pure products.
80%
Stage #1: With sodium hydride In mineral oil at 90℃; for 0.0833333 h;
Stage #2: at 115℃; for 6 h;
Example 1 Preparation of Compound 1; IPrOH Step A - Synthesis of Compound 1 bTo Me2COe (9mL) was added NaH (60percent dispersion in oil, 2.52g, 1.51mmol) and the solution was heated to 9O0C for 5min. To the solution α- tetralone (4.0Og, 27.4mmol) in Me2COa (9mL) was added and the solution was stirred at 1150C for 6h. Allowed to cool, added MeOH (0.9mL), added 3M HCI (93mL), transferred to sep funnel, extracted with ether, washed with sat. aq. NaHCψ3, washed with H2O, washed with brine, dried (MgSO4), filtered, and concentrated. Crude product was purified by flash column chromatography to yield compound 1b (4.5g, 80percent).
64% at 80℃; for 0.333333 h; Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
Sodium hydride (1.26 g, 36.75 mmol, 0.73 equiv, 70percent) was added in several batches to a mixture of 3,4-dihydronaphthalen-1(2H)-one (7.3 g, 50.00 mmol, 1.00 equiv) and dimethyl carbonate (50 mL).
The resulting solution was stirred for 20 min at 80° C.
The reaction was quenched by the addition of 150 mL of water/ice, then extracted with 3*100 mL of ether.The organic layers were combined and washed with 1*50 mL of brine, dried over anhydrous sodium sulfate, and concentrated in vacuo.
The residue was purified by silica gel column chromatography eluting with petroleum ether.
This provided 6.5 g (64percent) of methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate as a white solid.
LC-MS: (ES, m/z): 205 [M+H]+
1H-NMR (300 MHz, CDCl3, ppm): 12.40 (s, 0.5H), 8.07-7.16 (m, 4H), 3.83-3.78 (m, 3H), 3.66-3.61 (m, 0.5H), 3.07-2.79 (m, 2H), 2.60-2.37 (m, 2H)

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  • 8
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  • 14
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 28, p. 8589 - 8593
  • 15
  • [ 1829-28-3 ]
  • [ 7442-52-6 ]
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  • 16
  • [ 1829-28-3 ]
  • [ 6742-26-3 ]
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  • 17
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  • 18
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